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Highland Park Vacation Rentals

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Check prices for these dates

In two weeks
Dec 5 - Dec 7
In two months
Jan 16 - Jan 18
In three months
Feb 13 - Feb 15
In four months
Mar 13 - Mar 15

Vacation Rentals in Highland Park

Front of property - evening/night
Level Chicago – Old Town

Aparthotel in Downtown Chicago

4.0 star property
9.0 out of 10, Wonderful, (384)
"Property was clean, centrally located with wonderful staff. Will definitely stay again."
United States
Michelle
Level Chicago – Old Town
Private kitchen
River West, Third Floor Chicago by 747 Lofts

Aparthotel in West Town

2.0 star property
9.0 out of 10, Wonderful, (17)
"Overall solid property, I will return."
United States
Fletcher
The price is P3,798
P8,315 total
includes taxes & fees
Nov 30 - Dec 1
River West, Third Floor Chicago by 747 Lofts
Living area
Wrigleyville Suites

Aparthotel in Lakeview

2.0 star property
9.6 out of 10, Exceptional, (25)
"Excellent location and very clean! Would stay again!"
United States
Jacob
The price is P6,962
P8,173 total
includes taxes & fees
Nov 25 - Nov 26
Wrigleyville Suites
Exterior
Historic Oak Park Residence

Apartment in Oak Park

2.0 star property
9.6 out of 10, Exceptional, (12)
"Absolutely awesome "
United States
Erik
Historic Oak Park Residence
Private kitchen
The Gem Museum Suites

Aparthotel in Downtown Evanston

3.5 star property
9.4 out of 10, Exceptional, (96)
"Great stay. The studio is small but has everything necessary."
United States
Julia
The price is P10,713
P12,265 total
includes taxes & fees
Nov 30 - Dec 1
The Gem Museum Suites
Free WiFi
Logan Square SRO Hotel

Aparthotel in Logan Square

2.0 star property
Logan Square SRO Hotel
Interior
Walk to Wrigley Field! Townhouse w/ Pool Table

Apartment in Lakeview

3.0 star property
The price is P12,755
P35,435 total
includes taxes & fees
Dec 2 - Dec 3
Walk to Wrigley Field! Townhouse w/ Pool Table
Exterior
Chicago Third Floor Studio by 747 Lofts

Aparthotel in West Town

2.0 star property
9.6 out of 10, Exceptional, (5)
"Cute little studio that was clean. There was a nice size kitchen and was close to our activities in the West loop of Chicago. There was also assistance with parking located in the lofts."
United States
Jennifer
Chicago Third Floor Studio by 747 Lofts
Exterior
River West, Second Floor Chicago by 747 Lofts

Aparthotel in West Town

2.0 star property
9.6 out of 10, Exceptional, (4)
"I need to somewhere to stay for a night in Chicago and found this place. It had a varying level of reviews but found the property more the suitable for what I paid. Easy to follow instructions to get in, clean, and convienent. They even provide ear plugs to drown out the sounds of the city."
United States
Anonymous traveler
River West, Second Floor Chicago by 747 Lofts
Private kitchen
Chicago Second Floor Studio by 747 Lofts

Aparthotel in West Town

2.0 star property
8.8 out of 10, Excellent, (13)
"Great location, convenient to downtown and blue line to airport. Everything necessary in unit, comfortable temperature and full kitchen with unique grocery store nearby."
United States
Barbara
Chicago Second Floor Studio by 747 Lofts
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Highland Park Hotel Reviews

Level Chicago – Old Town

Level Chicago – Old Town

10/10 Excellent
"We always love staying here. Such great service and nice accommodations. "
Janet 3-night trip
Posted 2 days ago
Level Chicago – Old Town

Find out more about Highland Park

Search for holiday rentals in Highland Park on Expedia! You can easily find your home rentals, villas, holiday apartments in Highland Park using one of the methods below:

  • View our selection of featured holiday rentals in Highland Park
  • Use the map to find apartments and other holiday homes in the Highland Park neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Highland Park while they last

Look no further and take a look at our great range of rental properties in Highland Park!

Frequently asked questions

Are there vacation rentals in Highland Park?

Yes, there are vacation rentals near well known points of interest in Highland Park, or you can choose a secluded option if you're looking for relaxation. The shops and live music are just a few reasons why travelers like Highland Park. Allow lots of time to check out the gardens and restaurants during your visit.

How many vacation rentals are there in Highland Park?

With 5 Expedia vacation rentals, you're sure to find just the right place for your Highland Park stay.

What can I see and do in Highland Park?

Enjoy the outdoors at Lake Michigan and Chicago Botanic Garden, or simply take in cultural attractions like Ravinia Park and Ravinia Pavilion. Other popular places to visit in the area include Naval Base Great Lakes and Wrigley Field.

What are vacation rentals like in Highland Park?

Vacation rentals are privately owned properties you can stay in for several days or more in Highland Park. Vacation rentals feature amenities like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can provide a sense of privacy away from public hotel elevators and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for family trips or small group gatherings.